30,481

Windham County, VT Homes

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  • /29

    $200,000 Sold Oct 10, 2025

    • Land
    • 34 Acres
    • $5,882 per Acre
    • 465 Days On Market

    0 Hillside Dr Unit 4998188, Wilmington, VT 05363

    Discover Your Private Vermont Retreat – 34 Acres of Possibility and PeaceA rare opportunity awaits to own an expansive 34.0-acre parcel offering tremendous privacy, breathtaking views, and endless potential. Nestled amidst rolling topography with picturesque stone walls and a network of historic trails, this unique property invites exploration and inspiration at every turn. Two potential

    Monique White Deerfield Valley Real Estate

    0 Hillside Dr Unit 4998188, Wilmington, VT 05363
    • /35

      Est $312,857 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,092 Sq Ft

      7 Allison Ln, Vernon, VT 05354

      7 Allison Ln, Vernon, VT 05354
  • /3

    $275,000

    • 4 Beds
    • 2 Baths
    • 2,000 Sq Ft

    2173 Vermont 8a, Whitingham, VT 05361

    4 bedroom 2 bath home located on 4.7 acres. Has a ground level access. Level parking and garden spots. There are huge White Pine trees surrounding this home. Showings delayed until September 29, 2025 to allow for cleaning. License to Sell is needed and in progress, Expected in October.

    Mark Yule BHG Masiello Brattleboro

    2173 Vermont 8a, Whitingham, VT 05361
  • /34

    $375,000 Sold Oct 09, 2025

    • 1,127 Sq Ft
    • $333/SF
    • 268 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1988

    27 Haymaker Ln Unit 9H, Wilmington, VT 05363

    Cozy convenience on Haystack Mountain adjacent to The Hermitage Club and just a short drive to Mount Snow and downtown Wilmington. This 2 bedroom/2 bathroom unit has an open living space perfect for entertaining and highlighted by the fieldstone fireplace ambiance to warm you apres ski/hike or snowshoe. The unit is being offered furnished and ready to enjoy this season and year round with access

    Cordelia Garofalo Deerfield Valley Real Estate

    27 Haymaker Ln Unit 9H, Wilmington, VT 05363
    • /40

      Est $686,145 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,273 Sq Ft

      116 Lily Pond Rd, Vernon, VT 05354

      116 Lily Pond Rd, Vernon, VT 05354
  • /40

    $425,000

    • 2 Beds
    • 2 Baths
    • 1,386 Sq Ft

    152 Our Rd, Putney, VT 05346

    Delayed Showings - OPEN HOUSE Sat 9/20 from 10am to noon. Log Home Retreat on 4.7 Acres in Westminster, VT. Tucked back on a quiet road, is this welcoming 2-bedroom, 2-bath log home set on 4.7 private acres. A circular driveway brings you to the home, where a broad front porch invites you to slow down and take in the surroundings.Inside, you’ll find new flooring throughout

    Morriah Adams BHG Masiello Brattleboro

    152 Our Rd, Putney, VT 05346
  • /22

    $407,000 Sold Oct 08, 2025

    • 1,400 Sq Ft
    • $291/SF
    • 6 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1970

    7 Wanderer Rd Unit 7, Stratton, VT 05155

    Check out this location! Excellent proximity to the Stratton Base Lodge, Village and the Stratton Training and Fitness Center. This 3 bedroom, 2 bath Wanderer Chalet CO-OP has been beautifully updated. The large open floor plan on the main level is a comfortable gathering space with a fireplace and nicely upgraded kitchen. With fresh paint, renovated baths and new floors throughout this CO-OP is

    Dan McKenna Cummings & Co

    7 Wanderer Rd Unit 7, Stratton, VT 05155
    • /35

      Est $307,296 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,909 Sq Ft

      672 Hucklehill Rd, Vernon, VT 05354

      672 Hucklehill Rd, Vernon, VT 05354
  • /35

    $34,900

    • 1 Bed
    • 2 Baths
    • 745 Sq Ft

    341/43 Qtr.4,89 Grand Summit Way, Dover, VT 05356

    Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? This sleep 6 unit consists of two adjoining units; Studio unit (341) Queen murphy bed, kitchenette, full bathroom . Hotel unit (343) Two king beds, full bathroom. Units are located on the third floor mountain side of the hotel. Lock out units have the benefit of using the unit as a whole or stay in one side and rent the other

    Kelly Agrillo Southern Vermont Realty Group

    341/43 Qtr.4,89 Grand Summit Way, Dover, VT 05356
  • /56

    $350,000 Sold Oct 08, 2025

    • 1,004 Sq Ft
    • $349/SF
    • 5 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1967

    1077 Grassy Brook Rd, Brookline, VT 05345

    Nestled in the woods on a double lot totaling 10 acres along Grassy Brook Road, this charming one-bedroom, one-bathroom cabin offers the perfect blend of rustic comfort and natural beauty. Inside, the open living space is anchored by a Hearthstone woodstove, creating a warm and inviting atmosphere throughout the seasons. Enjoy the soothing sound of the brook just outside your door. Whether

    Claire Renaud Berkley & Veller Greenwood Country

    1077 Grassy Brook Rd, Brookline, VT 05345
    • /60

      Est $510,858 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,856 Sq Ft

      434 Scott Rd, Vernon, VT 05354

      434 Scott Rd, Vernon, VT 05354
  • /6

    $49,000

    • Land
    • 10.2 Acres
    • $4,804 per Acre

    0 Kurn Hattin Rd, Putney, VT 05346

    Discover the potential of this 10.2 acre lot nestled in the scenic hills of Westminster. With road frontage on a paved, town maintained road and easy access to I-91, this property offers both privacy and convenience. Located in an accessible area with a peaceful, wooded setting, it’s an ideal opportunity to own a piece of Vermont’s natural beauty.

    Rebecca Hiam Southern Vermont Realty Group

    0 Kurn Hattin Rd, Putney, VT 05346
  • /2

    $345,000 Sold Oct 07, 2025

    • 1,120 Sq Ft
    • $308/SF
    • 10 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1986

    154 Reed Rd, Chester, VT 05143

    Nature surrounds this charming cabin-style home, tucked into the woods and overlooking a peaceful pond. Privately situated, the home features an open-concept living area with a vaulted ceiling, inviting in natural light and offering views of the water. Step outside to a brand-new deck that extends your living space outdoors. The cozy kitchen is both functional and full of character, with

    Jessica Landers Barrett and Valley Associates Inc.

    154 Reed Rd, Chester, VT 05143
    • /34

      Est $453,112 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,160 Sq Ft

      458 Hazel Hill Rd, Townshend, VT 05353

      458 Hazel Hill Rd, Townshend, VT 05353
  • /42

    $1,150,000

    • 3 Beds
    • 3 Baths
    • 2,121 Sq Ft

    4 Hardwood Hill, Stratton, VT 05360

    Welcome to your mountain retreat in the exclusive TreeTop community at Stratton Resort. This upscale 3 level, 3 BR, 3 BA + bonus loft room townhome offers the perfect blend of alpine charm & modern comfort. Perched on the mountain with panoramic vistas, enjoy year-round views from your private stone patio & spacious deck. Step outside & take advantage of ski-back access right to your door, plus a

    Kim Morgan-Wohler Wohler Realty Group

    4 Hardwood Hill, Stratton, VT 05360
  • /15

    $190,000 Sold Oct 07, 2025

    • 802 Sq Ft
    • $237/SF
    • 9 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1980

    84 Signal Pine Rd, Putney, VT 05346

    Located just outside the Village of Putney, this privately sited home features 7.70 +/- acres of trees and meadow along with a pond area that's currently overgrown but could potentially be reclaimed for your enjoyment or just appreciating nature. The structure itself needs rehab as it's been stripped down to studs and needs attention inside and outside. However the location is great being close

    A.J. Bellville Bellville Realty

    84 Signal Pine Rd, Putney, VT 05346
    • /16

      Est $387,806 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,325 Sq Ft

      964 State Forest Rd, Townshend, VT 05353

      964 State Forest Rd, Townshend, VT 05353
  • /31

    $33,500

    • 1 Bed
    • 2 Baths
    • 709 Sq Ft

    145/47 Qtr.1,89 Grand Summit Way, Dover, VT 05356

    Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? This sleep 6 unit consists of two adjoining units; Studio unit (145) Queen murphy bed, kitchenette, full bathroom and a balcony. Hotel unit (147) Two queen beds, full bathroom and balcony. Units are located the mountain side of the hotel just down the hallway from the Spa, ski locker, health club and pool.. Lock out units

    Kelly Agrillo Southern Vermont Realty Group

    145/47 Qtr.1,89 Grand Summit Way, Dover, VT 05356
  • /27

    $950,000 Sold Oct 07, 2025

    • 3,000 Sq Ft
    • $317/SF
    • 49 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2006

    6B Foliage Ln, Dover, VT 05356

    Stunning renovated Kingswood townhome located conveniently between Mount Snow and the Hermitage Club Resorts in Southern VT. This beautifully updated 4 bedroom, 3.5 bath townhome was built in 2006 and renovated to a bold contemporary style in 2020 by the current owners. No expense was spared at making this a true dream getaway. Upon entry you are greeted by a large, functional mudroom complete

    Adam Palmiter Berkley & Veller Greenwood/Dover

    6B Foliage Ln, Dover, VT 05356
    • /33

      Est $289,634 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 946 Sq Ft

      60 Riverdale Rd, Townshend, VT 05353

      60 Riverdale Rd, Townshend, VT 05353
  • /43

    $445,000

    • 3 Beds
    • 2.5 Baths
    • 2,872 Sq Ft

    1587 Upper Holbrook Rd, Whitingham, VT 05361

    Set on 3 beautiful acres, this well-maintained 3-bedroom plus loft, 2 1/2 bath home is truly move-in ready. Enter through a spacious mudroom with a convenient back opening for bringing in firewood for the cozy wood stove in the living room. The open-concept kitchen and dining area provide plenty of room for entertaining, while a den/game room just off the living room with a bar area (4X8) offers

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    1587 Upper Holbrook Rd, Whitingham, VT 05361
  • /23

    $400,000 Sold Oct 07, 2025

    • 1,750 Sq Ft
    • $229/SF
    • 357 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1988

    43 1st Ln Unit 28, Wilmington, VT 05363

    Beautiful updated condo overlooking the 1st green at the Haystack Golf Club, as well as the mountains and sunsets beyond. This lovely private unit sits right on one of the best courses in New England, and is a short drive from the village of Wilmington, nearby lakes, and Mount Snow and Hermitage Club ski resorts. The interior features a large open living space with vaulted ceilings, updated vinyl

    Adam Palmiter Berkley & Veller Greenwood/Dover

    43 1st Ln Unit 28, Wilmington, VT 05363
    • /19

      Est $431,943 Not Listed For Sale

      • 1 Bed
      • 1,243 Sq Ft

      12 Depot Rd, Townshend, VT 05353

      12 Depot Rd, Townshend, VT 05353
  • /30

    $295,000

    • 3 Beds
    • 2 Baths
    • 1,328 Sq Ft

    876 Vermont Route 100, Wilmington, VT 05363

    Great location for full-time local residents or seasonal visitors. Easy access from Route 100. Nice yard and solid house. This is a comfortable 3-bedroom house with a living room, kitchen, and dining room! Centrally located and easily accessible. Please come see it!

    Tony Tribuno Skihome Realty

    876 Vermont Route 100, Wilmington, VT 05363
  • /50

    $260,000 Sold Oct 07, 2025

    • Land
    • 0.7 Acre
    • $371,429 per Acre
    • 19 Days On Market

    184 W Lake Rd, Wilmington, VT 05363

    Rare Lake Raponda Gem – Private Dock, Fire Pit, and More!Welcome to your dream lakefront playground on beautiful Lake Raponda!Private Dock – Enjoy swimming, kayaking, and boating.Fire Pit on the Deck – Perfect for cozy evenings with lake viewsBoat house.Private & Peaceful Setting – Nestled in nature with year-round access.

    Rich Caplan Deerfield Valley Real Estate

    184 W Lake Rd, Wilmington, VT 05363
    • /40

      Not Listed For Sale

      • 8 Beds
      • 6 Baths
      • 4,790 Sq Ft

      3031 Vt Route 30, Townshend, VT 05353

      3031 Vt Route 30, Townshend, VT 05353
  • /32

    $675,000

    • 3 Beds
    • 3 Baths
    • 2,216 Sq Ft

    12 Three Streams Way, Wilmington, VT 05363

    Beautiful 2006 chalet in the Chimney Hill community just a short drive from the Mount Snow Ski Resort and village Wilmington. This meticulous turn key home has been completely renovated and upgraded, and sits on a on a private lot in the Chimney Hill community on a quiet side road with access to snowmobile trails and winter views. Inside is a gorgeous great room space with vaulted ceilings and

    Adam Palmiter Berkley & Veller Greenwood/Dover

    12 Three Streams Way, Wilmington, VT 05363
  • /2

    $305,000 Sold Oct 06, 2025

    • 1,917 Sq Ft
    • $159/SF
    • 89 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1841

    152 Main St, Grafton, VT 05146

    Motivated Seller! This charming home in Grafton is ready for its next chapter! Centrally located next to the MKT market, offering easy access to the post office, town offices, library, school, inn, church, and local shops. With spacious and bright rooms, the home welcomes you into a main foyer that features a living room and study as its two front rooms. A dining room adjoins the living room and

    Jessica Landers Barrett and Valley Associates Inc.

    152 Main St, Grafton, VT 05146
    • /40

      Est $350,372 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,498 Sq Ft

      456 Grafton Rd, Townshend, VT 05353

      456 Grafton Rd, Townshend, VT 05353
  • /28

    $449,000

    • 3 Beds
    • 2 Baths
    • 1,510 Sq Ft

    49 West Rd, Wilmington, VT 05363

    Lovely renovated chalet at the bottom of the Chimney Hill community with easy access to trails, hiking, lakes, and nearby Mount Snow. This lovely private parcel sits in the easily accessible lower section with nice seclusion and views out the rear, affording nice privacy yet with all the conveniences of community living. The interior boasts an open concept living space with natural light and

    Adam Palmiter Berkley & Veller Greenwood/Dover

    49 West Rd, Wilmington, VT 05363
  • /2

    $266,000 Sold Oct 06, 2025

    • 1,440 Sq Ft
    • $185/SF
    • 6 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1930

    637 Wiswall Hill Rd, Townshend, VT 05353

    Discover your perfect Vermont escape in this cozy two-story cabin nestled on a sweet, level acre. Whether you're looking for a weekend getaway or a full-time residence, this home offers the ideal blend of rustic charm and everyday functionality. The lower level welcomes you into an open-concept guest or living space, with convenient access to utilities and a fenced-in shaded area—perfect for pets

    Jessica Landers Barrett and Valley Associates Inc.

    637 Wiswall Hill Rd, Townshend, VT 05353
    • /44

      Est $298,596 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,080 Sq Ft

      556 Stratton Arlington Rd, West Wardsboro, VT 05360

      556 Stratton Arlington Rd, West Wardsboro, VT 05360
  • /36

    $529,000

    • 3 Beds
    • 2.5 Baths
    • 2,044 Sq Ft

    11 Dutchman Ln Unit 4A, Wilmington, VT 05363

    This 3-bedroom plus loft, 2.5-bath end unit townhouse is in Powderhorn Village. The entrance boasts a mudroom, leading to a dining area adjacent to a fully equipped kitchen, complemented by a convenient powder room and living space with a wood-burning fieldstone fireplace. Access to an oversized deck and a bonus room with a hot tub and a private shower. Ascend to the second floor to find the

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    11 Dutchman Ln Unit 4A, Wilmington, VT 05363
  • /26

    $714,000 Sold Oct 06, 2025

    • 4,932 Sq Ft
    • $145/SF
    • 135 Days On Market
    • 18 Beds
    • 8 Baths
    • Built 1900

    29 Canal St, Brattleboro, VT 05301

    High cash flow 100% occupied 8 unit located in downtown Brattleboro. This property was recently renovated and is being listed at a 11% cap and an annual Net Operating Income estimated at north of ~$80K (12% cap without management fees). The property features an attractive mix of unit types and sizes including 4x rarely available oversized 3br, 2x2br and 2x1br A new owner can step into to this

    Michael Gilman 3GEN Real Estate Inc

    29 Canal St, Brattleboro, VT 05301
    • /35

      Est $195,459 Not Listed For Sale

      • 5 Beds
      • 1.5 Baths
      • 2,751 Sq Ft

      3 Granger St, Bellows Falls, VT 05101

      3 Granger St, Bellows Falls, VT 05101
  • /11

    $795,000

    • 4 Beds
    • 3 Baths
    • 3,409 Sq Ft

    633-635 Vermont Route 100, Stratton, VT 05360

    Great family compound or use one and rent the other. There are 2 homes on this property with direct access to VAST and the National Forest and `1.6 miles to the North entrance of Mt. Snow. Great opportunity with an excellent rental history. Both houses have full walk-out daylight lower levels, 2 decks and a hot tub at each home. Both homes were remodeled in 2014 including new roofs, windows and

    Ginny Read Read Realty LTD

    633-635 Vermont Route 100, Stratton, VT 05360
  • /55

    $396,500 Sold Oct 06, 2025

    • 1,958 Sq Ft
    • $203/SF
    • 177 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1980

    112 Breezy Acres Dr, Vernon, VT 05354

    Set on a beautifully sunlit, spacious lot, this classic Vermont home offers the perfect balance of comfort, functionality, and charm. Tucked in a quiet neighborhood, the property features a generous layout with thoughtful updates throughout. Inside, enjoy fresh new carpet and paint, brand new energy-efficient windows, a new dishwasher and electric range, enhancing both aesthetics and

    Kristen Ziter Taylor Brattleboro Area Realty

    112 Breezy Acres Dr, Vernon, VT 05354
    • /40

      Est $384,040 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 3,206 Sq Ft

      6 Hapgood St, Bellows Falls, VT 05101

      6 Hapgood St, Bellows Falls, VT 05101
  • /59

    $275,000

    • 2 Beds
    • 1 Bath
    • 715 Sq Ft

    81 Parish Hill Rd, Newfane, VT 05345

    Nestled in the hills of South Newfane, Vermont, this off-grid property offers the perfect balance of seclusion, recreation, and comfort. Set on 22.32± acres of mixed timberland, the land features a meandering creek, wildlife habitat, and excellent hunting opportunities for deer and turkey. A 715 sq. ft. cabin, approximately 80% complete, serves as the centerpiece of the property. Built with a

    Chad Bruyette Whitetail Properties Real Estate, LLC

    81 Parish Hill Rd, Newfane, VT 05345
  • /28

    $350,000 Sold Oct 06, 2025

    • 1,768 Sq Ft
    • $198/SF
    • 31 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1950

    177 Fairview St, Brattleboro, VT 05301

    Ta Da! This is it! This diamond in the rough was built for the owner in 1950 and has been in the family ever since! The kitchen is huge, large enough for the traditional kitchen table, or a new kitchen island. True, it is vintage, but lots of cabinets and countertop for cooking and open to both living and dining for great parties. The living room is 26 ft long and room for everyone with big

    Christine Lewis Brattleboro Area Realty

    177 Fairview St, Brattleboro, VT 05301

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